Boron trifluoride etherate → HCID 58197608, 화합물

HRID 473003

반응식

HRID 473003 반응식
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[CH2:12])[C:6]2=[O:11].[CH2:13]=[C:14]([O:17][Si](C)(C)C)[CH:15]=[CH2:16].B(F)(F)F.CCOCC>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5]1([CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)[C:6]2=[O:11]

참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 5546572-(Trimethylsiloxy)-1,3-butadieneHCID 58198117HCID 58198117, 화합물

생성물 1

HCID 58197608HCID 58197608, 화합물수율 52.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-fluoro-2-methylene-2,3-dihydro-1H-inden-1-one (249b) (3.71 g, 22.9 mmol) and (buta-1,3-dien-2-yloxy)trimethylsilane (5.2 mL, 29.8 mmol) in DCM (200 mL) at 0° C., there was added BF3.Et2O (0.5 mL dropwise. The resulting solution was stirred at 0° C. for another 30 min, quenched with MeOH (0.3 mL), warmed to room temperature, acidified with 2N HCl aqueous solution (15 mL) and extracted with DCM (10 mL×4). The combined organic layers were dried over Na2SO4, filtered and evaporated, and the residue was purified by flash chromatography (0 to 50% EtOAc/Hexane) to give 4′-fluorospiro[cyclohexane-1,2′-indene]-1′,4(3′H)-dione (249c) (2.77 g, 49%). LC-MS tR=1.41 min in 3 min chromatography, MS (ESI) m/z 233 [M+H]+.

후처리

  1. customquenched with MeOH (0.3 mL)
  2. temperaturewarmed to room temperature
  3. extractionextracted with DCM (10 mL×4)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue was purified by flash chromatography (0 to 50% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-c94d4ddb6dce4f5c957b8a592b55aa4a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633212B2

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